Summer of Sabrina Carpenter: Hitting No. 1 on the Charts, Getting Advice From Best Friend Taylor Swift and What Barry Keoghan Really Thinks About Her Lyrics
Counterpoint, a record store in Los Angeles’ Franklin Village, is probably not the first place one would expect to find Sabrina Carpenter on a sunny Monday afternoon — flipping through a stack of vintage Playboys, no less. The chart-dominating singer-songwriter is sipping a Yerba Mate while she oohs and ahhs at the blond bombshells of various yesteryears when a bright-blue cover featuring a pouty-faced model catches her eye.
“I love the faces of the ’60s and ’90s — old Hollywood, flirty and fun,” Carpenter says. “This is definitely the vibe of my album.”
Surely, she must know she has the face too, right? The instant-vintage portraits accompanying her two smash summer singles, “Espresso” and “Please Please Please,” have been ubiquitous since the former’s release in April, and she channels a similar Marilyn Monroe-inspired allure on the cover of her forthcoming album, “Short n’ Sweet,” due Aug. 23, as well as in the imagery for her first North American arena tour, which starts next month.
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She’s just returned from a hectic promotional jaunt through Europe, but today Carpenter seems dead set on digging through every aisle of this vinyl emporium. After pausing on Charli XCX’s “Brat” (“Love it!”), Olivia Newton-John’s “Soul Kiss” and Beyoncé’s “Lemonade,” she spies Connie Francis’ 1958 album “Who’s Sorry Now?”
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“Connie Francis is amazing and super underrated,” she says, admiring the cover photo. “Oh, my God, she’s beautiful. She’s really serving.” On July 2, 1960, a 21-year-old Francis became the first female artist to land a No. 1 song on the Billboard Hot 100 singles chart with “Everybody’s Somebody’s Fool.” Almost exactly 64 years later, on June 29, 2024, the 25-year-old Carpenter achieved her first No. 1 with “Please Please Please,” after reaching No. 3 the previous week with “Espresso” (which may have missed the top spot, but on Aug. 5 became the third-fastest song to reach a billion streams on Spotify). The hoped for but unexpectedly stratospheric chart success of the singles has built anticipation for her album to a near fever pitch.
“I’m so happy I finished this album before any of the songs came out,” Carpenter says. “Not that I think I would have let [the singles’ success] get in my head. But I really do think sometimes you can’t help but write from a different perspective after experiencing certain life events. I’m trying to avoid calling this ‘my dream album,’ because I don’t think I would have been able to dream up this set of songs a couple years ago.”
The songs show a seasoning that comes with experience, particularly “Please Please Please” and its hilarious video, which stars her real-life paramour, actor Barry Keoghan, and is written from the perspective of a woman who loves her man but is just about done with his bullshit. For all the pop frothiness of the songs and the candy-flossed imagery, there’s a savvy undercurrent of sass and grit: Both “Espresso” and “Please Please Please” have prominent f-bombs and innuendos in the lyrics.
But maybe not that much sass and grit. After a pause, Carpenter preemptively adds with a smile, “I’m not posing for Playboy — just to be clear.”
While Carpenter was considered a Disney princess for years, her transition from child actor to pop star — a perilous leap that has felled many before her — has been slow, steady and intentional. She admits that she sometimes feels like a new artist, even though she’s about to release her sixth album.
Born and raised in Quakertown, Pa., Carpenter moved to California with her family as a preteen. Her two older sisters, Shannon and Sarah, attended performing arts high schools and introduced her to an early influence — the 2008 musical “13,” starring a pre-Nickelodeon Ariana Grande (whom Carpenter would open for just a few years later). Carpenter showed precocious talent, and her family began taking her to auditions.
“I got a manager — the same one I have now — and he was very realistic,” she recalls. “He said, ‘We’ll send you out for things — no promise that they’re even going to see your tape.’ But then, not to brag, I booked one of the first things I ever went for”: an episode of “Law & Order” in which Carpenter played a victim of abuse by a sex-trafficking ring — at the ripe old age of 11.
“It was such a sad plotline,” she says. “I was just fascinated by all of it. I had spent so much time with adults that I just knew how to talk to them. Now all my friends are my age, but when I was younger, I was always working with adults. I just always knew what to say and how to act.”
At 12, she began a parallel career in music, signing with Disney’s Hollywood Records at the same time she landed the role of Maya in the Disney-produced “Boy Meets World” spinoff series, “Girl Meets World.” Despite the workload that came with pursuing both careers, “I wasn’t, like, grinding and working for hours on end as a child,” she recalls, “but I always felt I had a point to prove.”
Her longtime friend and vocal coach Eric Vetro says, “Not only did she have a great voice for a 12-year-old, she also had an incredibly mature attitude about what she wanted to achieve in her career and how she was going to accomplish it. I worried that she might burn out from starting so young, but those fears evaporated when I witnessed her working harder than ever year after year.”
After a few middling hit singles like “Thumbs” and “Why,” Carpenter released “Singular: Act II,” her fourth and final album for Hollywood, in the summer of 2019, shortly after she turned 20. Around the same time, she ended a yearlong legal battle with her former managers, who claimed they were owed compensation after she terminated their contract. The case was eventually dismissed, and she followed by releasing a tongue-in-cheek song called “Sue Me” that was certified gold and showed some of the burgeoning cheekiness that is blooming now.
“For the people who love those early records and listen to them, I love you for that,” she says. “But I personally feel a sense of separation from them, largely due to the shift in who I am as a person and as an artist, pre-pandemic and post-pandemic.”
Lockdown ended the first phase of Carpenter’s career with a thud, quashing her early 2020 Broadway debut in “Mean Girls” after just two performances. But, as it did for many people, the pandemic led her to a restart. She signed with Island Records, her current label, in January 2021 and the following year released “Emails I Can’t Send,” an introspective and honest coming-of-age album filled with lyrics inspired by real-life events and conflicts with famous peers, ex-boyfriends and even family.
On it, Carpenter references the narrative around a Gen-Z love triangle allegedly involving her and fellow Disney stars Joshua Bassett and Olivia Rodrigo. Although the full story has never been revealed, all three singers have released songs inspired by the situation — including Rodrigo’s 2021 breakthrough hit, “Drivers License” — and the ensuing scrutiny from fans and the media. For her part, Carpenter sings in “Because I Liked a Boy,” “Now I’m a homewrecker, I’m a slut / I got death threats fillin’ up semi trucks.” (She declines to discuss the situation further.)
On the album’s title track, Carpenter also touches on the suffering that accompanied her father’s infidelity toward her mother (though the timeline is unclear). “I am a daddy’s girl,” she says. “But my family has just gone through so much that now we’re all in a healing stage. As I’ve gotten older, I’ve started learning about men and relationships. I’m not perfect by any means, but it definitely makes you look at your parents differently.” She concludes: “‘Emails’ was hard to put out, but it marked the beginning of a really freeing and artistic time for me.”
It also became her highest-charting LP to date, reaching No. 23 and remaining on the Billboard 200 albums chart for 43 weeks and then spawning an 80-date international headlining tour.
Following that success, however, the media scrutiny has moved to her other relationships, including her friendship with Taylor Swift, on whose “Eras Tour” Carpenter was an opening act in Latin America, Australia and Singapore. One flash point was Carpenter’s ad campaign for Skims, the clothing company owned by Swift’s bitter rival, Kim Kardashian. While Carpenter has maintained that Swift was aware of the campaign and is fine with it, fans soon twisted that information into sentiments like “Asking for permission to do a campaign is crazy,” as one wrote on X.
The subject comes up in the record store when we notice that Swift’s latest offering, “The Tortured Poets Department,” is filed in the rock section. Without skipping a beat, Carpenter replies, “Well, Taylor is a rock star!” She goes on: “She’s just such a gangster with all of it. No matter what people are saying, everything that I’ve ever seen her tackle, she’s done so with grace. The posts about me having to ‘ask for her permission’ — no. She’s one of my best, best friends, and we grab dinner or text and catch up like you would with your best friend.”
She nods to the mentorship she’s received from Swift and others as she grapples with her own rapidly rising fame. “It’s so cool for me to get a perspective on this whole process from her and the community of artists that I feel I’m close to — to get advice from them on stuff that you can’t just ask the internet,” she says. “We’re always playing each other our [music], and whenever I start to think, ‘Maybe I’ll get on Twitter and say something about this,’ I’m always like, ‘Maybe I’ll write a song instead.’”
However, she’s more careful in what she reveals about her relationship with Keoghan, although she opens up a bit when asked about the “Basic Instinct”-inspired music video for “Please Please Please,” the lyrics of which say the problematic boyfriend is an actor.
“He loved the song. He’s obsessed with the lyrics, and I’m so grateful for that,” she says. “I don’t want to sound biased, but I think he’s one of the best actors of this generation. So getting to see him on the screen with my song as the soundtrack made the video better and all the more special.”
Later, as we pass an astrology book in the store, she says, “Barry’s a Libra, and so is my sister. They’re very different, but they have similarities. I tend to gravitate towards Leos as well.” Her smile fades before she adds, “My dad’s a Capricorn, so maybe that’s not the direction for my future.”
Carpenter describes her upcoming record “Short n’ Sweet” as “the hot older sister” of “Emails.” “It’s my second ‘big girl’ album; it’s a companion but it’s not the same. When it comes to having full creative control and being a full-fledged adult, I would consider this a sophomore album.”
That maturity and professionalism is co-signed by her collaborators. “She was always 10 minutes early to every session and still is,” says co-writer Steph Jones. “It was just a matter of timing for her [success], because everyone she’s worked with describes themselves as an instant fan.”
“Sabrina has become a sister to me,” adds Amy Allen, who co-wrote “Espresso” and “Please Please Please” (as well as Top 10 hits this year for Tate McRae and Justin Timberlake). “We spend hours on end talking about any and everything. She makes me laugh ’til I cry. She truly makes me a better writer every time I’m in the room with her.”
The effort has paid off. “Espresso”’s indelible hooks and nonsensical catchphrase, “That’s that me, espresso,” have been quoted and memed by everyone from Cardi B to Brooke Shields — and even inspired an ad for the Paris Olympics. The song, along with stellar performances at Coachella and on “Saturday Night Live,” effectively launched “Sabrina Summer,” which Swift proudly predicted in the first week of June.
However, Carpenter says, “I was completely alone in wanting to release ‘Espresso.’ Not so much from my immediate team. But when it came to ‘the powers above,’” she air-quotes, “there was a lot of questioning behind whether it made sense. But they trusted me in the end, and I was happy that I believed in myself at that moment.”
“It’s no accident that everything is falling into place the way she always wanted,” says Island Records co-CEO Imran Majid. “Sabrina’s instincts and creative vision are incredible. She’s always thinking 10 steps ahead of the market.” Co-CEO Justin Eshak adds, “She’s an inspiration for her fans, collaborators and all of us — she’s one of this generation’s most important artists.”
Musically, “Short n’ Sweet” takes inspiration from ’90s pop, but fans shouldn’t expect the sort of real-time lyrical reveals that have become a trademark of other artists.
“It feels easier to write about things that happened in the past, or that haven’t happened yet,” she says. “My producers tell me I’m beating a dead horse because I’ll write a song three years after I last spoke to the person who inspired the lyric. Also,” she adds with a laugh, “and this is my ego talking, but I would be honored to find out someone wrote a song about me, even if it was bad. Like, ‘I triggered you enough to write a song? Go off!’”
Although Carpenter’s music focus has meant an “unwarranted break” from acting, she’s always looking at scripts in the hopes of securing a spot in a musical or an original film, although she says “a lot of them sound like five other already released movies.” She’s waiting for one that feels right.
“I’m 900 inappropriate jokes away from being a Disney actor, but people still see me that way,” she says. “I’m always extremely flattered to be grouped in with the other women and girls who I’ve idolized and looked up to who came from that, but I feel very distant from it.”
By the time we exit the store, Carpenter is clutching a bag full of records: two Beatles solo albums — “Ringo” and Paul McCartney’s “Red Rose Speedway”; an old Island Records promotional compilation, “because it’s my label”; several randos because she liked the artwork; and, finally, a $100 copy of Interview magazine with Keanu Reeves on the cover for her sister. She gushes about the forthcoming vinyl edition of her own album, which includes a non-streaming bonus track (there are also cassette and CD variants with alternative covers). The retro-inspired package was designed by herself, her sister Sarah, Dannah Gottlieb and Chase Shewbridge. “I spent so much time working on the vinyl; I think it’s one of my favorite things I’ve ever made,” she says.
Sarah is coming to pick her up, but first we decide to venture to a neighboring Van Leeuwen ice cream shop. At the entrance, Carpenter stops dead in her tracks when she sees what’s taped to the door: a blown-up poster of her own face, advertising the brand’s limited-edition “Espresso” flavor.
“Oh God,” groans the singer who has been coasting unrecognized (or at least not approached) in the closed-up record store. “How embarrassing is that?”
Additional reporting by Jem Aswad
